Ethyl Acetoacetate → HCID 13799835, compound

HRID 1762472Notes

Reaction equation

HRID 1762472 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.[C:13](OCC)(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>>[C:13]([O:1][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 122503792-(1,3-dihydro-2H-isoindol-2-yl)ethanol

Product 1

HCID 13799835HCID 13799835, compoundYield 22%

Procedure

A solution of 4.67 g (0.029 mol) of 2-(2-hydroxyethyl) isoindoline and 3.72 g (0.029 mol) of ethyl acetoacetate was heated at 100°-110° C. under nitrogen for 36 hours. Ethanol was removed with nitrogen flow during the course of the reaction. The mixture was subjected to flash chromatography (silica gel, 1:1 ethylacetate/petroleum ether) to give 1.54 g (22%) of a dark oil. NMR (CDCl3) δ 2.2 (3H, s), 2.94 (2H, t), 3.4 (2H, s), 3.9 (4H, s), 4.24 (2H, t), 7.04 (4H, s)

Workup

  1. customEthanol was removed with nitrogen flow during the course of the reaction

Sources & evidence

ORD record
ord-00fdfce0c0ed4868845387979c045061
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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